Interesting Ways to Start Online Conversations (That AREN'T "Hi" or "Hey")

"I'm tired of using the typical hi or hey to start conversations on chat apps. What are some interesting and unique ways to start chats with women?"

This all-too-common question has come up enough times that I thought it was worth answering. And I'm going to be blunt.

If you’re “starting conversations” with the “typical hey or hi,” it means one thing:

You’re not chatting me because you have something to say. You’re chatting me for the sake of chatting me.

That’s boring.

If someone sends me a message like that, I don’t answer. I mean, maybe if I happen to be sitting around doing absolutely nothing. But, like... I'm a play expert. That almost literally never happens. 

I literally stop to smell the roses. Or... peach blossoms?

If you want to have a conversation with someone, have a conversation. SAY SOMETHING.

This is where a lot of so-called "nice guys" run into trouble. They're nice... but that's it. They have nothing else to offer. No ideas. No opinions. No thoughts or invitations. 

If you want to have a lively conversation -- one that, perhaps, turns into a friendship or a relationship -- you have to be "nice" as a minimum requirement. But if that's all you are, to quote Sondheim, "You're not good, you're not bad, you're just nice."

Be more. Say more. Say something! 

For example, here are the messages I’ve used to initiate the last however many online and mobile conversations I’ve had:

• Hey, new bestie! What’s the deal with the tournament this weekend?
• Yo, man. Let’s play ball on Wednesday.
• OMG so guess who won the songwriting contest? (Hint: it was not me)
• Whaddduuuup, motherfucker??!!! It’s Holy Week. Wanna do some Jesus Christ Superstar karaoke on Thursday?
• OMG you’ll never guess who I’ve been playing basketball with for years without even knowing it. I’ll give you a hint: he’s contributed to Nobel Prize-winning economics research and I cite him to my students ALL the time.
• Check out this crazy article about Big Sur — apparently it’s an island and a ghost town right now. WANNA GO SEE IT?????? 
• Hi, Jeff. I saw the video you posted of your new album. You’re clearly a “real” songwriter, and I am not. Can I pick your brain about something?
• OMG, guess whose birthday party I went to last night? Hint: HE thinks HE'S your best friend, when we both know clearly *I* am.
• Hey, so... FRIZZZZZZZZZZ?* 

*Which I hoped/assumed the person would understand to mean "let's play ultimate frisbee"

See how, when I message people, it’s because I actually want to SAY something? It’s not because I’m bored. It’s not because I want to hit on them. It’s because we have a common interest, a mutual friend, or a plan to do something together.

Each of these conversations ended up being super interesting, and I ended up learning a lot. If you want to start a conversation with someone, have something to say or ask.
Because, again, “hi” and “hey” are boring, and I typically ignore such messages.

So say, as someone asked me recently, you don't actually know the person. You're messaging someone online that you don't know.

First of all, just... why?

If it's Facebook, the message is going to go into her "other" folder, and she'll never see it. If it's online dating, she will have written a whole little profile that you could... you know. Read? Determine if you have a common interest? Or, if not, ask her a question about something she mentioned?

Most women aren't wild about "spray and pray" (or is it "prey"?) messages. If you could have sent the exact same message to everyone on the dating app, chances are it won't catch her attention. If you can't take the time to read her profile before reaching out, why should she take the time to reply?